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Tuscany Road Trip: Florence & Siena

For 6-Nights: Explore Tuscany’s Treasures by Car – A Scenic Road Trip Through Renaissance Art, Medieval Streets, Grand Cathedrals & Historic Squares: Florence & Siena.

Road Trip

Trip Code: #11209

What's included?

All Flights

Hotels

Rental Cars

Flexibility Policy

Expert trip manager

All taxes & fees

Best Price Guarantee

Customize and Book with an Expert

(647) 694-5673

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Road TripNew DealsTrip Code: #11209

Best Price Guarantee

Customize and Book with an Expert

(647) 694-5673

Offline

Dates and Prices

Select a day to go to next step

Day By Day Itinerary

7-days itinerary trip visiting 1 country and 2 cities

Day 1 Welcome to Florence, Italy!
Arrive at Florence Airport, pick up your rental car, and drive to your hotel. Check in and take some time to relax and settle in.

Suggestion For The Day:

Explore at the Cathedral of Santa Maria del Fiore (Duomo).

Climb the Brunelleschi's Dome for panoramic views of the city.

After visiting the cathedral, head to the Baptistery of San Giovanni and Giotto’s Campanile. Enjoy lunch in a nearby trattoria and spend the afternoon wandering through the Piazza della Signoria to see the Palazzo Vecchio and Loggia dei Lanzi. Finish the day with dinner at a restaurant in the Santa Croce area.
Day 2Florence: Scenic Views & Renaissance Masterpieces
Suggestion For The Day:

Visit San Miniato al Monte for stunning city views, then head to Piazzale Michelangelo. Explore the Basilica of Santo Spirito and its Michelangelo masterpiece.

Enjoy a Tuscan meal in the Santo Spirito district.

In the afternoon, discover the Bargello Museum and the historic Officina Profumo-Farmaceutica di Santa Maria Novella. Stroll through the charming San Niccolò neighborhood.

Relax with a sunset aperitivo by the Arno and enjoy a Bistecca alla Fiorentina for dinner.
Day 3Florence: Art, History & Artisan Treasures
Suggestion For The Day:

Visit the Uffizi Gallery in the morning to view masterpieces by Botticelli, Michelangelo, and Leonardo da Vinci.

Have lunch at a nearby café.

In the afternoon, stroll across the Ponte Vecchio and explore the Oltrarno district, known for its artisan shops and local crafts.

End the day with dinner in the Oltrarno area, where you can enjoy a traditional Tuscan meal.
Day 4Drive to Siena
Start your day with an early breakfast in Florence before driving approximately 1 hour and 15 minutes to Siena. Upon arrival, drop off your luggage at your accommodation and begin exploring this vibrant city.

Suggestion For The Day:

Begin your journey in Piazza del Campo, the heart of Siena, where you can admire the unique shell-shaped square and soak in the medieval atmosphere. Climb the Torre del Mangia for breathtaking panoramic views before exploring the Palazzo Pubblico & Civic Museum, home to remarkable frescoes like Lorenzetti’s Allegory of Good and Bad Government.

After lunch, visit the stunning Siena Cathedral (Duomo di Siena), known for its intricate marble interiors and the Piccolomini Library. Continue to the Baptistery of San Giovanni & Crypt to admire Renaissance frescoes and the impressive baptismal font. Conclude your day with a leisurely dinner in the historic center.
Day 5Siena: Saints, Traditions & Tuscan Delights
Suggestion For The Day:

Start your morning at the Basilica of San Domenico, home to relics of Saint Catherine of Siena. Stroll through the charming streets to the Sanctuary of Saint Catherine, a peaceful spot dedicated to the city’s patron saint.

After lunch, wander through the Contrade neighborhoods to learn about the traditions of the Palio horse race. Visit the Santa Maria della Scala, a former hospital turned museum, featuring frescoes and archaeological treasures.

End your day with a wine-tasting experience at a traditional enoteca, paired with Tuscan delicacies.
Day 6Siena: Medieval Villages & Sunset Strolls
Suggestion For The Day:

Embark on a scenic morning drive to Monteriggioni, a perfectly preserved medieval walled village just 20 minutes from Siena. Walk along the fortress walls for stunning countryside views.

Return to Siena for lunch, then visit the Fortezza Medicea, a peaceful spot perfect for a relaxed stroll.

End your trip with a sunset walk along Via di Città, admiring elegant palaces and hidden corners before enjoying a farewell dinner at a local trattoria.
Day 7Drive Back to Florence & Return Flight Home
Start your day by driving back to Florence (1 hour 15 minutes).

Depending on your flight schedule, you might have time to explore some highlights.

As your departure time approaches, drive to the airport, return your rental car, and check-in for your flight.

We hope you had an incredible time in Italy - happy travels and until next time!

Itinerary presented is a suggestion and the length of stay may vary. All tours are suggestions unless clearly stated.

Why We Love This Deal

A Perfect Blend of Art, History & Tuscan Charm:
This 7-night Tuscany road trip immerses you in the heart of Italy’s most iconic region - from Florence’s breathtaking Renaissance masterpieces to Siena’s medieval streets steeped in tradition. Experience historic piazzas, grand cathedrals, and rolling countryside all woven into one unforgettable journey.

Freedom to Explore at Your Own Pace:
With a rental car included and a thoughtfully designed itinerary, you have the flexibility to customize your adventure. Take scenic detours through vineyards, stop at quaint villages, and savor spontaneous moments in Tuscany’s stunning landscapes.

Handpicked Authentic Experiences:
Discover not only Florence’s world-famous art and architecture but also Siena’s hidden corners and local traditions. Enjoy authentic Tuscan cuisine - from Florence’s legendary bistecca alla Fiorentina to Siena’s delicious pici pasta, paired with world-class wines.

Effortless Planning, Maximum Enjoyment:
Everything is pre-arranged - from flights and handpicked hotels to rental car and daily highlights - so you can simply relax and focus on savoring the magic of Tuscany.

Ideal for Art Lovers, History Buffs & Foodies:
Whether you’re a first-time visitor or returning explorer, this itinerary balances iconic sights with authentic experiences, making it the perfect Tuscan getaway.

Available Experiences

Optional

Location: Florence

Sightseeing Tours: Highlights of Tuscany: Siena, San Gimignano, Chianti, Pisa - with Lunch

Additional cost applies

Optional

Location: Florence

Food & Wine: Pasta Cooking Class with Unlimited Wine

Additional cost applies

Optional

Location: Florence

Sightseeing Tours: Florence in one day: Uffizi Gallery, Michelangelo’s David and City Guided Walking Tour

Additional cost applies

Optional

Location: Florence

Sightseeing Tours: Tuscany Vintage Vespa Tour from Florence (2 people)

Additional cost applies

Optional

Location: Florence

Food & Wine: Chianti Authentic Experience with two Wine Tastings and two charming Villages

Additional cost applies

Optional

Location: Florence

Sightseeing Tours: Florence Duomo Skip-the-Line Guided Tour with Priority Entrance

Additional cost applies

Optional

Location: Florence

Food & Wine: Florence Gelato Making Class, Small Group Tour

Additional cost applies

Optional

Location: Florence

Food & Wine: Florence Dinner Tour: Truffle, Florentine Steak & Fine Wines

Additional cost applies

Optional

Location: Florence

Food & Wine: Florence Sunset Tour

Additional cost applies

Optional

Location: Florence

Food & Wine: Florence Central Market Tour

Additional cost applies

Optional

Location: Florence

Food & Wine: The Other Side of Florence Tour

Additional cost applies

Optional

Location: Florence

Food & Wine: Authentic Florence Pasta Making Class

Additional cost applies

Optional

Location: Florence

Food & Wine: Pizza & Gelato Making Class in Oltrarno

Additional cost applies

Optional

Location: Florence

Food & Wine: Tuscany Truffle Hunt: A Culinary Adventure

Additional cost applies

Things to Know

About the Destinations

Important Information

Flexibility Policy

Travel Support Anytime Anywhere

When booking a trip with us, you don’t just get our local experts' support and a superb travel experience, you also get the guarantee of full flexibility on our end. We know plans can change, and when that’s the case, we’re here to help!

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Tuscany Road Trip: Florence & Siena

Trip Code: #11209

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Dates and Prices

Itinerary

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